Trifluoroacetic acid → HCID 67976197, compound

HRID 2168189Notes

Reaction equation

HRID 2168189 reaction equation
FC(F)(F)C(O)=O.CC([N:12]([CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[C:23]3[C:30]([CH3:31])=[CH:29][NH:28][C:24]=3[N:25]=[CH:26][N:27]=2)[CH2:18][CH2:17]1)C(=O)[O-])(C)C>>[CH3:31][C:30]1[C:23]2[C:22]([N:19]3[CH2:20][CH2:21][CH:16]([NH2:12])[CH2:17][CH2:18]3)=[N:27][CH:26]=[N:25][C:24]=2[NH:28][CH:29]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86710201HCID 86710201, compound

Product 1

HCID 67976197HCID 67976197, compound

Procedure

Trifluoroacetic acid (TFA) (5 ml) was added to a solution of 1,1-dimethylethyl[1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4-piperidinyl]carbamate D10 (580 mg, 1.313 mmol). The mixture was stirred at room temperature during one hour. The solvent was evaporated and purified using and SCX cartridge (5 g). The cartridge was washed sequentially with MeOH and then Ammonia in MeOH (0.5M and 1M). The washings with Ammonia in methanol 0.5M and 1M were combined and evaporated to give D11a (280 mg) as a white solid. LCMS [M+H][email protected] mins (2 minute run).

Workup

  1. customThe solvent was evaporated
  2. custompurified
  3. washThe cartridge was washed sequentially with MeOH
  4. washThe washings with Ammonia in methanol 0.5M and 1M
  5. customevaporated
  6. customto give D11a (280 mg) as a white solid
  7. customLCMS [M+H][email protected] mins (2 minute run)

Sources & evidence

ORD record
ord-da06294c642c4324b818349d5ead07de
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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